JPH04164057A - Production of 3-cyano-3,5,5-trimethylcyclohexanone - Google Patents
Production of 3-cyano-3,5,5-trimethylcyclohexanoneInfo
- Publication number
- JPH04164057A JPH04164057A JP2285816A JP28581690A JPH04164057A JP H04164057 A JPH04164057 A JP H04164057A JP 2285816 A JP2285816 A JP 2285816A JP 28581690 A JP28581690 A JP 28581690A JP H04164057 A JPH04164057 A JP H04164057A
- Authority
- JP
- Japan
- Prior art keywords
- isophorone
- hydrocyanic acid
- solvent
- ipcn
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- JJDFVIDVSCYKDS-UHFFFAOYSA-N 1,3,3-trimethyl-5-oxocyclohexane-1-carbonitrile Chemical compound CC1(C)CC(=O)CC(C)(C#N)C1 JJDFVIDVSCYKDS-UHFFFAOYSA-N 0.000 title claims abstract description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 56
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 13
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 239000002994 raw material Substances 0.000 abstract description 5
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000000806 elastomer Substances 0.000 abstract description 2
- 239000003822 epoxy resin Substances 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 239000011527 polyurethane coating Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- -1 aminomethyl-3,5,5-trimethylcyclohexanone Chemical compound 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- IKGRHMKNUHTLIL-UHFFFAOYSA-N cyanic acid 3,5,5-trimethylcyclohex-2-en-1-one Chemical compound O=C1C=C(CC(C)(C)C1)C.N#CO IKGRHMKNUHTLIL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、３−シアノ−３，５，５−トリメチルシクロ
ヘキサノン（以下、ＩＰＣＮと略記する）の製造法に関
するものである。さらに詳しくは、塩基性触媒と溶媒１
，３−ジメチル−２−イミダゾリジノン（以下、ＤＭＩ
と略記する）の存在下で、イソホロンと青酸から生産性
の高いＩＰＣＮの製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a method for producing 3-cyano-3,5,5-trimethylcyclohexanone (hereinafter abbreviated as IPCN). For more details, see Basic Catalysts and Solvents 1
, 3-dimethyl-2-imidazolidinone (hereinafter referred to as DMI
The present invention relates to a highly productive method for producing IPCN from isophorone and hydrocyanic acid in the presence of (abbreviated as ).
ＩＰＣＮは、アミノ化と水素添加を経て１−アミノ−３
−アミノメチル−３，５，５−トリメチルシクロヘキサ
ノンに導かれ、エポキシ樹脂用硬化剤や高級エラストマ
ー、ポリウレタン塗料原料である１−インシアナト−３
−（イソシアナトメチル）−３，５，５−トリメチルシ
クロヘキサノンに導かれる産業上有用な基礎原料であっ
て、近年、需要が急速に増加してきている。IPCN is converted to 1-amino-3 through amination and hydrogenation.
-1-incyanato-3 is derived from aminomethyl-3,5,5-trimethylcyclohexanone and is a curing agent for epoxy resins, high-grade elastomers, and raw material for polyurethane paints.
It is an industrially useful basic raw material derived from -(isocyanatomethyl)-3,5,5-trimethylcyclohexanone, and its demand has been rapidly increasing in recent years.
（従来の技術）
従来より、イソホロンと青酸を原料とするＩＰＣＮの製
造法は知られている。例えば、Ｗ、Ｆ、Ｗｈｉｔｙａｏ
ｒｅおよびＣ，Ｒ，Ｒ，Ｒｏｂｅｒｔ、 Ｊ、Ｏｒｇ、
Ｃｈｅｍ、＋ １３＋３１ （１９４８）では、イソホ
ロンとシアン化ナトリウムを、メタノールと水と氷酢酸
の混合溶媒中で、室温において１週間反応させることに
より、約４５％の収率でＩＰＣＮを得ている。しかしな
がら、この方法は低収率であり、かつ、反応日数を要す
るため、工業的方法としては全く問題にならない。(Prior Art) A method for producing IPCN using isophorone and hydrocyanic acid as raw materials has been known. For example, W, F, Whityao
re and C,R,R,Robert, J,Org,
Chem, +13+31 (1948), IPCN was obtained in about 45% yield by reacting isophorone and sodium cyanide in a mixed solvent of methanol, water, and glacial acetic acid at room temperature for one week. However, this method has a low yield and requires several days of reaction, so it is not a problem at all as an industrial method.
また、特公昭４０−７４８６号公報によれば、固体担体
に付着させたアルカリ触媒上に、イソホロンに対し青酸
が約１０重量％以下のイソホロン−青酸混合物を供給し
て、ＩＰＣＮを連続的に合成している。しかしながら、
この方法は、多量の未反応イソホロンの回収を必要とす
るため、工業的方法としては問題がある。Furthermore, according to Japanese Patent Publication No. 40-7486, IPCN is continuously synthesized by supplying an isophorone-cyanic acid mixture containing about 10% by weight or less of hydrocyanic acid to isophorone on an alkali catalyst attached to a solid carrier. are doing. however,
This method is problematic as an industrial method because it requires recovery of a large amount of unreacted isophorone.
さらに、西独特許１，０８５，８７１号明細書によれば
、ジメチルアセトアミド溶媒中でアルカリ金属塩を触媒
とし、イソホロンと青酸とを反応させてＩＰＣＮを合成
している。しかしながら、この方法によるＩＰＣＮの収
率は約７０％と低く、溶媒の回収に多大の経費を必要と
する。Further, according to West German Patent No. 1,085,871, IPCN is synthesized by reacting isophorone and hydrocyanic acid in a dimethylacetamide solvent using an alkali metal salt as a catalyst. However, the yield of IPCN by this method is as low as about 70%, and a large amount of expense is required for recovering the solvent.
さらにまた、西独特許１，２４０，８５４号明細書によ
れば、メタノールを溶媒としてアルカリ金属塩触媒の存
在下に、イソホロンと青酸を反応させてＩＰＣＮを合成
している。しかしながら、この方法は、特開昭５７−１
１６０３８号公報によると多量の青酸重合物が生成し、
ＩＰＣＮの収率は約８０％と低いものである。Furthermore, according to West German Patent No. 1,240,854, IPCN is synthesized by reacting isophorone and hydrocyanic acid in the presence of an alkali metal salt catalyst using methanol as a solvent. However, this method is
According to Publication No. 16038, a large amount of hydrocyanic acid polymer is produced,
The yield of IPCN is as low as about 80%.
次に、特開昭５７−１１６０３８号公報によれば、無機
の塩基性触媒とグリコール類の存在下に青酸の重合物の
副生を避けるため、大過剰のイソホロンに青酸を反応さ
せてＩＰＣＮを合成している。しかしながら、未反応の
イソホロンを大量に回収する必要があり、工業的には問
題がある。Next, according to JP-A-57-116038, in order to avoid the by-product of polymerization of hydrocyanic acid in the presence of an inorganic basic catalyst and glycols, a large excess of isophorone is reacted with hydrocyanic acid to produce IPCN. It is being synthesized. However, it is necessary to recover a large amount of unreacted isophorone, which poses an industrial problem.
さらには、特開昭６１３３１５８号公報によれば、ジア
ザ−ビシクロ−アルケン類（有機塩基触媒）の存在下で
イソホロンに青酸を反応させてＩＰＣＮを合成している
。しかしながら、この方法は、高価な触媒を多量に使用
し、この触媒の回収を行うことが必要で、工業的に行う
には問題がある。Furthermore, according to JP-A-6133158, IPCN is synthesized by reacting isophorone with hydrocyanic acid in the presence of diaza-bicyclo-alkenes (organic base catalyst). However, this method requires the use of a large amount of expensive catalyst and the recovery of this catalyst, which poses problems for industrial use.
（発明が解決しようとする課題）
こうした背景から、イソホロンと青酸からＩＰＣＮを工
業的に収率良く安価に製造する方法が望まれている。(Problems to be Solved by the Invention) Against this background, a method for industrially producing IPCN from isophorone and hydrocyanic acid with high yield and at low cost is desired.
（ｔ！［題を解決するための手段）
本発明者らは、この方法について鋭意検討を重ね、溶媒
にＤＭＩを用いて塩基性触媒存在下で反応を行わせると
、イソホロン／青酸モル比として等モルで反応が進み、
高収率でＩＰＣＮが得られることを見出し、本発明をな
すに至った。(t! [Means for solving the problem) The present inventors have conducted extensive studies on this method, and found that when the reaction is carried out in the presence of a basic catalyst using DMI as a solvent, the isophorone/cyanic acid molar ratio is The reaction proceeds with equimolar
It was discovered that IPCN can be obtained in high yield, and the present invention was completed.
すなわち、本発明のＩＰＣＮの製造方法は、塩基性触媒
とＤＭＩの存在下に、イソホロンと青酸とを温度６０〜
１６０℃で反応させることを特徴とするものである。That is, in the method for producing IPCN of the present invention, isophorone and hydrocyanic acid are heated in the presence of a basic catalyst and DMI at a temperature of 60 to
It is characterized by being reacted at 160°C.
本発明において用いられる塩基性触媒としては、例えば
、ナトリウム、カリウム等のアルカリ金属、ナトリウム
、カリウム等のアルカリ金属の水酸化物、シアン化物、
炭酸化物、酸化物、アルコラード等、公知の塩基性触媒
が用いられる。触媒の使用量は特に制限はないが、使用
するインホロンに対し０．０５〜１．５重量％の範囲と
するのがよい。Examples of the basic catalyst used in the present invention include alkali metals such as sodium and potassium, hydroxides and cyanides of alkali metals such as sodium and potassium,
Known basic catalysts such as carbonates, oxides, and alcolades are used. The amount of the catalyst to be used is not particularly limited, but it is preferably in the range of 0.05 to 1.5% by weight based on the inholon used.
溶媒であるＤＭＩの使用量は、反応に用いるイソホロン
量と重量比で５〜５０％の範囲とするのがよい。５％以
下では反応が進みに＜＜、反応完結に長時間を要し好ま
しくない。また、５０％を超えると溶媒の回収が増加し
、コスト上好ましくない。The amount of DMI used as a solvent is preferably in the range of 5 to 50% by weight relative to the amount of isophorone used in the reaction. If it is less than 5%, the reaction will not progress and it will take a long time to complete the reaction, which is not preferable. Moreover, if it exceeds 50%, the recovery of the solvent will increase, which is not preferable in terms of cost.
反応に用いるイソホロンと青酸の割合は、モル比でイソ
ホロン／青酸が０．８〜１．５、好ましくは１前後であ
る。０．８未満では未反応青酸が多量に残り、後処理が
多くなり、また、青酸ロスも多くなる。１．５を超える
と未反応イソホロン量が多くなり、回収のための経費が
増え好ましくない。The molar ratio of isophorone to hydrocyanic acid used in the reaction is 0.8 to 1.5, preferably around 1. If it is less than 0.8, a large amount of unreacted hydrocyanic acid remains, resulting in increased post-treatment and increased prussic acid loss. If it exceeds 1.5, the amount of unreacted isophorone increases, which increases the expense for recovery, which is not preferable.
反応温度は６０〜１６０℃、好ましくは１００〜１４０
℃である。６０℃未満では反応が遅く、また、１６０℃
を超えると副反応が増え、収率が低下する。The reaction temperature is 60-160°C, preferably 100-140°C.
It is ℃. The reaction is slow below 60°C, and
Exceeding this will increase side reactions and reduce the yield.
反応時間は特に制限するものではないが、１〜１０時間
で目標の反応率を得ることができる。Although the reaction time is not particularly limited, the target reaction rate can be obtained in 1 to 10 hours.
本発明の方法を実施するに当たっては、インホロン、塩
基性触媒および溶媒の混合物を加熱攪拌し、これに青酸
を供給し反応させてＩＰＣＮを製造することができる。In carrying out the method of the present invention, IPCN can be produced by heating and stirring a mixture of inphorone, a basic catalyst, and a solvent, and supplying hydrocyanic acid to the mixture for reaction.
青酸の供給法としては、液体青酸を滴下する方法、ある
いは不活性ガスをキャリヤーとして使用した青酸をフィ
ードする方法などが用いられる。As a method of supplying hydrocyanic acid, a method of dropping liquid hydrocyanic acid, a method of feeding hydrocyanic acid using an inert gas as a carrier, etc. are used.
（実施例）
以下、本発明を実施例により具体的に説明するが、本発
明は、この実施例のみに限定されるものではない。(Examples) Hereinafter, the present invention will be specifically explained using Examples, but the present invention is not limited only to these Examples.
実施例で明らかなように、反応に供するイソホロン／青
酸モル比が１ではＩＰＣＨの収率が格段に高く、工業的
に実施する上で多大な効果がある。As is clear from the examples, when the molar ratio of isophorone/cyanic acid used in the reaction is 1, the yield of IPCH is extremely high, and this has a great effect on industrial implementation.
実施例１
攪拌機、冷却管、温度針および冷却管付滴下ロートを備
えた反応装置に、イソホロン５２９．１重量部と炭酸カ
リウム６．６重量部、ＤＭ１４７゜３重量部を仕込み、
攪拌しなから油浴上で加熱した。滴下ロートに青酸１１
０．３重量部を入れ、反応液を１１０℃に保ちつつ、攪
拌下に青酸を４時間かけて滴下した（イソホロン／青酸
モル比＝１．０）。青酸滴下後、１１０℃で１時間反応
を行ったのち、８０％リン酸８．５重量部を添加した。Example 1 529.1 parts by weight of isophorone, 6.6 parts by weight of potassium carbonate, and 3 parts by weight of DM147.
It was heated on an oil bath without stirring. Hydrocyanic acid 11 in the dropping funnel
0.3 parts by weight was added thereto, and while the reaction solution was kept at 110° C., hydrocyanic acid was added dropwise over 4 hours with stirring (isophorone/cyanic acid molar ratio = 1.0). After dropping hydrocyanic acid, the reaction was carried out at 110° C. for 1 hour, and then 8.5 parts by weight of 80% phosphoric acid was added.
未反応の青酸をＮ２ガスを通して０．０１％以下に除去
した。室温に冷却後、塩を濾別し、反応液をガスクロマ
トグラフィーで分析を行った。Unreacted hydrocyanic acid was removed to 0.01% or less by passing N2 gas. After cooling to room temperature, the salt was filtered off, and the reaction solution was analyzed by gas chromatography.
その結果、イソホロンの反応率は８８％で、ＩＰＣＮへ
の選択率は９４％であり、ＩＰＣＨの収率は８３％であ
った。また、反応液を減圧蒸留して純度９９％のＩＰＣ
Ｎ５０２ｇを得た。As a result, the reaction rate of isophorone was 88%, the selectivity to IPCN was 94%, and the yield of IPCH was 83%. In addition, the reaction solution is distilled under reduced pressure to obtain IPC with a purity of 99%.
502 g of N was obtained.
比較例１
実施例１と同様の装置に、イソホロン５２８゜０重量部
と炭酸ナトリウム５．１重量部、溶媒としてエチレング
リコール３７．６重量部を仕込み、攪拌下に１１０℃の
温度で青酸１０２．９重量部を３．５時間にわたって滴
下して反応させた（イソホロン／青酸モル比＝１．０）
、滴下終了後、１１０℃で１時間反応を行ったのち、８
０％リン酸９．８重量部を添加した。未反応の青酸をＮ
。Comparative Example 1 Into the same apparatus as in Example 1, 528.0 parts by weight of isophorone, 5.1 parts by weight of sodium carbonate, and 37.6 parts by weight of ethylene glycol as a solvent were charged, and 102.0 parts by weight of hydrocyanic acid was added at a temperature of 110°C with stirring. 9 parts by weight was added dropwise over 3.5 hours to react (isophorone/cyanic acid molar ratio = 1.0)
After the completion of the dropwise addition, the reaction was carried out at 110°C for 1 hour, and then
9.8 parts by weight of 0% phosphoric acid was added. unreacted hydrocyanic acid with N
.
ガスを通して０．０１％以下に除去した。室温に冷却後
、塩を濾別し、反応液を分析した。その結果、イソホロ
ンの反応率は４７％で、ＩＰＣＮへの選択率は８８％で
あり、ＩＰＣＮの収率は４１％であった。It was removed to 0.01% or less by passing gas through it. After cooling to room temperature, the salts were filtered off and the reaction solution was analyzed. As a result, the reaction rate of isophorone was 47%, the selectivity to IPCN was 88%, and the yield of IPCN was 41%.
（ほか１名）(1 other person)
Claims (1)
度６０〜１６０℃で反応させ、３−シアノ−３，５，５
−トリメチルシクロヘキサノンを製造する方法において
、溶媒として１，３−ジメチル−２−イミダゾリジノン
を用いることを特徴とする３−シアノ−３，５，５−ト
リメチルシクロヘキサノンの製造法。In the presence of a basic catalyst and a solvent, isophorone and hydrocyanic acid are reacted at a temperature of 60 to 160°C to form 3-cyano-3,5,5
- A method for producing 3-cyano-3,5,5-trimethylcyclohexanone, the method comprising using 1,3-dimethyl-2-imidazolidinone as a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2285816A JPH04164057A (en) | 1990-10-25 | 1990-10-25 | Production of 3-cyano-3,5,5-trimethylcyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2285816A JPH04164057A (en) | 1990-10-25 | 1990-10-25 | Production of 3-cyano-3,5,5-trimethylcyclohexanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04164057A true JPH04164057A (en) | 1992-06-09 |
Family
ID=17696460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2285816A Pending JPH04164057A (en) | 1990-10-25 | 1990-10-25 | Production of 3-cyano-3,5,5-trimethylcyclohexanone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04164057A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0985659A1 (en) * | 1998-08-12 | 2000-03-15 | Basf Aktiengesellschaft | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| DE102010062603A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| DE102011077681A1 (en) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| CN109761855A (en) * | 2018-12-20 | 2019-05-17 | 万华化学集团股份有限公司 | A method of preparing isophorone diisocyanate |
| CN115433103A (en) * | 2022-10-09 | 2022-12-06 | 山东新和成维生素有限公司 | Synthesis method of isophorone nitrile |
-
1990
- 1990-10-25 JP JP2285816A patent/JPH04164057A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0985659A1 (en) * | 1998-08-12 | 2000-03-15 | Basf Aktiengesellschaft | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| DE102010062603A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for the preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| WO2012076317A1 (en) | 2010-12-08 | 2012-06-14 | Evonik Degussa Gmbh | Process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine |
| DE102011077681A1 (en) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| CN109761855A (en) * | 2018-12-20 | 2019-05-17 | 万华化学集团股份有限公司 | A method of preparing isophorone diisocyanate |
| US11939280B2 (en) | 2018-12-20 | 2024-03-26 | Wanhua Chemical Group Co., Ltd. | Method for preparing isophorone diisocyanate |
| CN115433103A (en) * | 2022-10-09 | 2022-12-06 | 山东新和成维生素有限公司 | Synthesis method of isophorone nitrile |
| CN115433103B (en) * | 2022-10-09 | 2023-08-18 | 山东新和成维生素有限公司 | Synthesis method of isophorone nitrile |
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